35951-28-1

Basic information

• Product Name: 2-CHLOROCYCLODODECANONE
• Synonyms: 2-CHLOROCYCLODODECANONE;2-Chloro-1-cyclododecanone;2-Chlorocyclododecane-1-one;2-Chlorocyclododecanon;Cyclododecanone, 2-chloro-
• CAS NO: 35951-28-1
• Molecular Formula: C₁₂H₂₁ClO
• Molecular Weight: 216.75
• Mol File: 35951-28-1.mol

Chemical Properties

• Melting Point: 59-60 °C
• Boiling Point: 327.1°C at 760 mmHg
• Flash Point: 189.4°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 0.000206mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2-CHLOROCYCLODODECANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROCYCLODODECANONE(35951-28-1)
• EPA Substance Registry System: 2-CHLOROCYCLODODECANONE(35951-28-1)

Safety Data

• Hazardous Substances Data: 35951-28-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 185, 1973 DOI: 10.1021/jo00941a054

InChI:InChI=1/C12H21ClO/c13-11-9-7-5-3-1-2-4-6-8-10-12(11)14/h11H,1-10H2

Upstream product

• 1501-82-2 cyclododecene 
• 3667-85-4 2-methanesulfonatecyclododecanone 
• 830-13-7 cyclododecanone 
• 121758-10-9 (phenylmethoxy)cyclododecane 
• 286-99-7 1,2-epoxycyclododecane 
• 19025-38-8 2-hydroxycyclododecanone 
• 73839-43-7 (E)-1-(trimethylsilyl)cyclododecene 
• 55314-44-8 [((E)-Cyclododec-1-enyl)oxy]-trimethyl-silane 
• 71365-98-5 1-Acetoxy-cis-cyclododecen 
• 1129-89-1 cis-cyclododecene 

Downstream Products

• 60060-41-5 3-methyl-7,8,9,10,11,12,13,14,15,15a-decahydro-6H-cyclododeca[e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 76331-08-3 2-methoxycyclododecanone 
• 42768-79-6 (1R,11S,12S,15R)-17-Oxa-tricyclo[9.4.1.1^12,15]heptadec-13-en-16-one 
• 99946-13-1 17-oxatricyclo<9.4.1.1^12,15>heptadec-13-en-16-one 
• 37609-23-7 2-ethenylcyclododecanone 
• 43086-65-3 2-chloro-1-vinylcyclododecanol 
• 42747-23-9 1-cycloundecyl-4-penten-1-one 
• 86173-53-7 2-Isopropenyl-1-vinyl-cyclododecanol 
• 35951-27-0 1,2-divinylcyclododecan-1-ol 
• 107569-28-8 12-cyanobicyclo<9.1.0>dodecan-12-ol 
• 79272-61-0 2,2-dibromo-12-chlorocyclododecanone 
• 79265-58-0 2,12-dibromo-2-chlorocyclododecanone 
• 41886-65-1 (E)-3-cyclododecenone 
• 53601-11-9 1,2-Epoxy-1-vinylcyclododecene 

Relevant articles and documents

Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate

An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.

A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant

α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).

Oxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide

The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.

Addition of NOCl to cyclic vinylsilanes: An unexpected reversal of regiochemistry

NOCl adds to cyclic vinylsilanes in a syn manner with NO+ bonding to the β-carbon and Cl- to the α-carbon, which is a reversal of the regiochemistry expected from the β-silicon effect. The adducts dimerize to a single diastereomer containing enantiomeric pairs and/or give secondary products on further reaction.

α-chlorination of ketones using p-toluenesulfonyl chloride

Treatment of a variety of ketones with lithium diisopropylamide followed by p-toluenesulfonyl chloride gives α-chloroketones in good yields. In addition, a polymer bound tosyl chloride reagent has also been shown to effect this transformation.

OXIDATION OF OLEFINS USING CHROMIC ANHYDRIDE-CHLOROTRIMETHYLSILANE. A CONVENIENT SYNTHESIS OF α-CHLORO KETONES.

Disubstituted internal olefins are oxidized selectively to α-chloro ketones in excellent yields from the reaction with chromic anhydride-chlorotrimethylsilane in carbon tetrachloride.

OXYCHLORINATION OF ALKENES BY CHLOROCHROMATE REAGENTS: A FACILE PREPARATION OF α-CHLOROKETONES, AND COMPETITION BY SUBSTITUENT-DIRECTED OXIDATION.

Cyanopyridinium chlorochromate effects a facile preparation of α-chloroketones from simple alkenes, cycloocta-1,5-diene and cyclododeca-1,5,9-triene; 1-methylcaclooct-4-en-1-ol undergoes oxidative cyclization.

SELECTIVE FAVORSKII REARRANGEMENT IN MACROCYCLIC RINGS

A mixture of 2,2-dibromo-12-chlorocyclododecanone (IIa) and 2,12-dibromo-2-chlorocyclododecanone (IIb) by Favorskii rearrangement gave selectively methyl 2-chloro-1-cycloundecene-1-carboxylate (IIIa).